CN116135862A - Heterocyclic compound, light-emitting device including the same, and electronic device - Google Patents

Heterocyclic compound, light-emitting device including the same, and electronic device Download PDF

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CN116135862A
CN116135862A CN202211418980.8A CN202211418980A CN116135862A CN 116135862 A CN116135862 A CN 116135862A CN 202211418980 A CN202211418980 A CN 202211418980A CN 116135862 A CN116135862 A CN 116135862A
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姜儒真
田美恩
秋昌雄
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Samsung Display Co Ltd
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    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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Abstract

The present invention relates to a heterocyclic compound, and a light-emitting device and an electronic device including the heterocyclic compound. The heterocyclic compound is represented by formula 1. Formula 1
Figure DDA0003941374050000011

Description

Heterocyclic compound, light-emitting device including the same, and electronic device
Cross Reference to Related Applications
The present application claims priority and benefit from korean patent application No. 10-2021-0158041 filed in the korean intellectual property office on day 11 and 16 of 2021, the entire contents of which are incorporated herein by reference.
Technical Field
One or more embodiments of the present disclosure relate to a heterocyclic compound, a light-emitting device including the heterocyclic compound, and an electronic device including the light-emitting device.
Background
Among the light emitting devices, the organic light emitting device is a self-emission device, has a wide viewing angle, high contrast, short response time, and excellent or appropriate characteristics in terms of brightness, driving voltage, and response speed, as compared with the related art devices, and produces a full color image.
The organic light emitting device may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied from the first electrode move toward the emission layer through the hole transport region, and electrons supplied from the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emissive layer to generate excitons. The excitons may transition from an excited state to a ground state, thereby generating light.
Disclosure of Invention
Aspects of one or more embodiments of the present disclosure relate to a heterocyclic compound, a light-emitting device including the heterocyclic compound, and an electronic device including the light-emitting device.
Additional aspects of embodiments of the disclosure will be set forth in part in the description which follows, and in part will be obvious from the disclosure, or may be learned by practice of the embodiments of the disclosure as presented.
According to one or more embodiments, the heterocyclic compound may be represented by formula 1:
1 (1)
Figure BDA0003941374030000021
2, 2
Figure BDA0003941374030000022
Wherein, in the formulas 1 and 2,
A 1 is C 3 -C 60 Carbocyclyl or C 1 -C 60 Heterocyclyl, and A 2 Is C 1 -C 60 A heterocyclic group,
L 1 to L 3 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
a1 to a3 may each independently be an integer selected from 0 to 3,
R 1 to R 3 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 )、-P(＝O)(Q 1 )(Q 2 ) Or a group represented by the formula 2,
n1 and n2 may each independently be an integer selected from 1 to 10,
n 1R in 1 1 N 2R 2 And R is 3 At least one of them may be a group represented by formula 2,
Ar 1 to Ar 3 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
* Indicating the bonding sites with adjacent atoms,
R 10a the method comprises the following steps:
Deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or a combination of one or more of them,
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof, or
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )，
Wherein Q is 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl, C 1 -C 60 C substituted by heterocyclyl or one or more combinations thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
According to one or more embodiments, a light emitting device includes a first electrode,
a second electrode facing the first electrode,
an interlayer between the first electrode and the second electrode and comprising an emissive layer, and
at least one heterocyclic compound represented by formula 1.
According to one or more embodiments, an electronic device includes a light emitting device.
Drawings
The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:
fig. 1 is a schematic view of a light emitting device according to an embodiment;
fig. 2 is a cross-sectional view of a light emitting device according to an embodiment; and is also provided with
Fig. 3 is a cross-sectional view of a light emitting device according to another embodiment.
Detailed Description
Embodiments will now be explained in more detail with reference to examples thereof in the accompanying drawings, wherein like reference numerals refer to like elements throughout, and a repetitive description thereof may not be provided. In this regard, the present embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the embodiments are described solely by reference to the accompanying drawings to explain aspects of the embodiments of the present disclosure. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. Throughout this disclosure, the expression "at least one of a, b, and c" indicates only a, only b, only c, both a and b, both a and c, both b and c, all a, b, and c, or variants thereof.
Aspects of embodiments of the present disclosure relate to heterocyclic compounds represented by formula 1:
1 (1)
Figure BDA0003941374030000041
2, 2
Figure BDA0003941374030000051
Wherein, in the formulas 1 and 2,
A 1 is C 3 -C 60 Carbocyclyl or C 1 -C 60 Heterocyclyl, and A 2 Is C 1 -C 60 A heterocyclic group. In an embodiment, A 2 May be C comprising at least one nitrogen atom 1 -C 60 A heterocyclic group.
In an embodiment, A 1 Can be phenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolyl benzoborolane, benzophospholane, indenyl, benzoxazolyl, benzogermanopyranenyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl dibenzoborolan, dibenzophospholanene, fluorenyl, dibenzosilol, dibenzogermanium heterocyclopenadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5, 5-dioxide, azaindolyl, azabenzoborolan, azabenzoselenophenyl, dibenzothiophene-5-oxide, and process for preparing the same azabenzophospholanenyl, azaindenyl, azabenzothiophenyl, azabenzogermanium cyclopentenyl, azabenzothiophenyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azabenzoborolidienyl, azadibenzophospholanenyl, azafluorenyl, azadibenzosilolyl, azabenzogermanium heterocyclopenadienyl, azadibenzothiophenyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophen-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophen-5, 5-dioxide, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthroline, pyrrolyl, pyrazole An aryl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzotriazole group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, a 5,6,7, 8-tetrahydroisoquinolyl group, or a 5,6,7, 8-tetrahydroisoquinolyl group.
A 2 Azadibenzoborol, azadibenzophosphol, azadibenzoborol azafluorenyl, azadibenzosilol, azadibenzogermyl, cyclopentenyl, and process for preparing the same azadibenzoborol, azadibenzophosphol, azafluorenyl, azadibenzosilol, azadibenzogermanium heterocyclopenadienyl, azadiphenyl Azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, and azaazainto-process for preparing the same aza-9H-fluoren-9-one, aza-dibenzothiophene-5, 5-dioxide, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthroline, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzotriazole, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl, or 5,6,7, 8-tetrahydroquinolinyl.
L 1 To L 3 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group.
In an embodiment, L 1 To L 3 Can each independently be unsubstituted or substituted with at least one R 10a Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolylIndolyl, benzoborolidinyl, indenyl, benzothiophenyl, benzosilol, benzogermanium heterocyclopenadienyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzoborolidinyl, fluorenyl, dibenzosilol, dibenzogermanium heterocyclopenadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluorene-9-onyl, dibenzothiophene-5, 5-dioxide, azaindolyl, azabenzoborolidinyl, azabenzophospholidinyl, azaindenyl, azabenzosilol, azabenzoguanenyl, azabenzoselenophenyl, azabenzofuranyl, azacyclopentadienyl, and the like azacarbazolyl, azadibenzoborol, azadibenzophosphol, azafluorenyl, azadibenzosilol, azagermyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene-5, 5-dioxide, azadiphenyl sulfide-5-oxide, azadiphenyl sulfide-5-one, azadiphenyl sulfide-5-oxide, azadiphenyl sulfide-3-one, and the like pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzotriazolyl, benzoxazolyl, benzotriazolyl, oxazolyl, thiazolyl, oxazolyl, and benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolyl or 5,6,7, 8-tetrahydroquinolinyl.
In an embodiment, L 1 To L 3 Can be represented by one of the formulas 3-1 to 3-41 each independently:
Figure BDA0003941374030000071
/>
Figure BDA0003941374030000081
wherein, in the formulas 3-1 to 3-41,
X 1 can be N or C (Z 3 )，
X 2 Can be N or C (Z 4 )，
X 3 Can be N or C (Z 5 )，
X 4 Can be N or C (Z 6 )，
Y 1 It may be either O or S,
Y 2 can be O, S, N (Z) 7 ) Or C (Z) 7 )(Z 8 )，
Z 1 To Z 8 Each independently can be:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or one or more combinations thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )，
Wherein Q is 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Respectively with Q as described herein 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 The same is true of the fact that,
e6 may be an integer selected from 1 to 6,
e7 may be an integer selected from 1 to 7,
e8 may be an integer selected from 1 to 8, and
* And each indicates a bonding site to an adjacent atom.
a1 to a3 may each independently be an integer selected from 0 to 3.
When a1 is 0, L 1 May not exist, and R 1 And A 1 Can be directly connected to each other via a single bond. When a1 is 0, L 1 Can exist as a single bond.
When a2 is 0, L 2 May not exist, and R 2 And A 2 Can be directly connected to each other via a single bond. When a2 is 0, L 2 Can exist as a single bond.
When a3 is 0, L 3 May not exist, and R 3 Can be directly connected with the nucleus through a single bond. Example(s)For example, when a3 is 0, L 3 Can exist as a single bond.
In embodiments, at least one of n1 a1, n2 a2, and a3 in formula 1 may be an integer of 1 or more. For example, a3 may be an integer of 1 or more.
In an embodiment, the sum of n1 a1, n2 a2, and a3 in formula 1 may be 2 or more.
R 1 To R 3 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 )、-P(＝O)(Q 1 )(Q 2 ) Or a group represented by formula 2.
n1 and n2 may each independently be an integer selected from 1 to 10.
n1 are: - (L) 1 ) a1 -R 1 May be the same or different from each other, and n2 are- (L) 2 ) a2 -R 2 May be the same or different from each other.
N 1R in 1 1 N 2R 2 And R is 3 At least one of them may be a group represented by formula 2.
Ar 1 To Ar 3 Can be hydrogen, deuterium, -F, -Cl-Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )。
* Indicating the bonding sites with adjacent atoms.
R 10a The method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or one or more groups thereofCombining;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )，
Wherein Q is 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently can be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl, C 1 -C 60 C substituted by heterocyclyl or one or more combinations thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
In an embodiment, the heterocyclic compound represented by formula 1 may be represented by formula 1-1:
1-1
Figure BDA0003941374030000111
Wherein, in the formula 1-1,
X 11 can be N or C (E 11 )，
X 12 Can be N or C (E 12 )，
X 13 Can be N or C (E 13 )，
X 14 Can be N or C (E 14 )，
X 21 Can be N or C (E 21 )，
X 22 Can be N or C (E 22 )，
X 23 Can be N or C (E 23 )，
X 24 Can be N or C (E 24 )，
E 11 Can be: - (L) 11 ) a11 -R 11 ，
E 12 Can be: - (L) 12 ) a12 -R 12 ，
E 13 Can be: - (L) 13 ) a13 -R 13 ，
E 14 Can be: - (L) 14 ) a14 -R 14 ，
E 21 Can be: - (L) 21 ) a21 -R 21 ，
E 22 Can be: - (L) 22 ) a22 -R 22 ，
E 23 Can be: - (L) 23 ) a23 -R 23 ，
E 24 Can be: - (L) 24 ) a24 -R 24 ，
L 11 To L 14 Can be independently from each other L 1 The description of (c) is the same,
a11 to a14 may each be independently the same as the description of a1,
R 11 to R 14 Can be each independently with R 1 The description of (c) is the same,
L 21 to L 24 Can be independently from each other L 2 The description of (c) is the same,
a21 to a24 may each be independently the same as the description of a2,
R 21 to R 24 Can be each independently with R 2 The description of (c) is the same,
L 3 、a3、R 3 and R is 10a Can be respectively with L described herein 3 、a3、R 3 And R is 10a The same is true of the fact that,
R 11 to R 14 、R 21 To R 24 And R is 3 At least one of them may be a group represented by formula 2, and
* Indicating the bonding sites with adjacent atoms.
In an embodiment, E 11 To E to 14 And E is 21 To E to 24 Optionally bonded to each other to form an unsubstituted or substituted group with at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 2 -C 30 A heterocyclic group.
In an embodiment, in formula 1-1,
R 3 can be a group represented by formula 2; or (b)
X 24 Can be C (E) 24 ) And R is 24 Can be a group represented by formula 2.
In an embodiment, X 11 Can be C (E) 11 )，X 12 Can be C (E) 12 )，X 13 Can be C (E) 13 )，X 14 Can be C (E) 14 )，X 21 Can be C (E) 21 )，X 22 Can be C (E) 22 )，X 23 Can be C (E) 23 ) And X is 24 Can be C (E) 24 )。
In an embodiment, the heterocyclic compound represented by formula 1-1 may be represented by formula 1-1 (a):
1-1 (a)
Figure BDA0003941374030000121
Wherein, in the formula 1-1 (a),
L 11 to L 14 A11 to a14, R 11 To R 14 、L 21 To L 24 A21 to a24, R 21 To R 24 、L 3 A3 and R 3 Each as described herein, and
R 11 to R 14 、R 21 To R 24 And R is 3 At least one of them may be a group represented by formula 2.
In an embodiment, in formula 1-1 (a), R 3 Can be a group represented by formula 2, or R 24 Can be a group represented by formula 2.
In an embodiment, the heterocyclic compound represented by formula 1-1 may be represented by formula 1-2:
1-2
Figure BDA0003941374030000131
Wherein, in the formula 1-2,
X 31 can be N or C (E 31 )，
X 32 Can be N or C (E 32 )，
X 33 Can be N or C (E 33 )，
X 34 Can be N or C (E 34 )，
X 35 Can be N or C (E 35 )，
E 31 Can be: - (L) 31 ) a31 -R 31 ，
E 32 Can be: - (L) 32 ) a32 -R 32 ，
E 33 Can be: - (L) 33 ) a33 -R 33 ，
E 34 Can be: - (L) 34 ) a34 -R 34 ，
E 35 Can be: - (L) 35 ) a35 -R 35 ，
X 11 To X 14 And X 21 To X 24 Each of which is the same as that described herein,
L 31 to L 35 Can be independently from each other L 3 The description of (c) is the same,
a31 to a35 may each independently be an integer selected from 0 to 2,
R 31 To R 35 Can be each independently with R 3 The description of (c) is the same,
R 11 to R 14 、R 21 To R 24 And R is 31 To R 35 At least one of them may be a group represented by formula 2, and
* Indicating the bonding sites with adjacent atoms.
In an embodiment, in formulas 1-2, X 31 To X 35 At least one of which may be N.
In embodiments, R 1 To R 3 Each independently can be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
c each substituted by 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or one thereofOr a combination of multiple;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C, each unsubstituted or substituted by 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, or azadibenzothiazyl). Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranylA group, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, azadibenzosilol, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or one or more combinations thereof;
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
A group represented by the formula 2,
wherein Q is 1 To Q 3 And Q 31 To Q 33 Each independently can be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl each of which is unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl, diphenylAnd thienyl or one or more combinations thereof.
In one or more embodiments, R 1 To R 3 Each independently can be:
hydrogen, deuterium, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
c each substituted by 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group: deuterium, -CD 3 、-CD 2 H、-CDH 2 、C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, or one or more combinations thereof;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C, each unsubstituted or substituted by 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, isoindolyl, indolyl, indazolyl, purinyl, carbazolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, or dibenzocarbazolyl: deuterium, -CD 3 、-CD 2 H、-CDH 2 、C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, isoindolyl, indolyl, indazolyl, purinyl, carbazolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ) Or one or more combinations thereof;
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 ) or-B (Q) 1 )(Q 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
A group represented by the formula 2,
wherein Q is 1 To Q 3 And Q 31 To Q 33 Each independently can be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthylcarbazolyl, dibenzofuranyl or dibenzothienyl each unsubstituted or substituted with: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or one or more combinations thereof.
In an embodiment, ar 1 To Ar 3 Each independently can be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
c each substituted by 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexeneA group, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or one or more combinations thereof;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C, each unsubstituted or substituted by 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, or azadibenzothiazyl). Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinylQuinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, azadibenzosilol, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or one or more combinations thereof; or (b)
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) And (2) and
Q 1 to Q 3 And Q 31 To Q 33 Each independently can be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl each of which is unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, and diBenzofuranyl, dibenzothienyl, or one or more combinations thereof.
In another embodiment, ar 1 To Ar 3 Each independently can be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
c each substituted by 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or one or more combinations thereof;
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
A group represented by one of the formulas 4-1 to 4-36:
Figure BDA0003941374030000171
/>
Figure BDA0003941374030000181
/>
Figure BDA0003941374030000191
wherein, in the formulas 4-1 to 4-36,
Y 41 can be O, S, N (Z) 45 )、C(Z 45 )(Z 46 ) Or Si (Z) 45 )(Z 46 )，
Z 41 To Z 46 Can be hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )，
e3 may be an integer selected from 1 to 3,
e4 may be an integer from 1 to 4,
e5 may be an integer selected from 1 to 5,
e6 may be an integer selected from 1 to 6,
e7 may be an integer selected from 1 to 7,
e9 may be an integer selected from 1 to 9,
Q 1 to Q 3 And Q 31 To Q 33 Each independently can be:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl each of which is unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or one or more combinations thereof, and
* Indicating the bonding sites with adjacent atoms.
In one or more embodiments, the heterocyclic compound represented by formula 1 may be selected from compounds 1 to 8, but embodiments of the present disclosure are not limited thereto:
Figure BDA0003941374030000211
the heterocyclic compound represented by formula 1 may have a structure in which at least one silol group is included in the core of the condensed heterocyclic nucleus (e.g., the core of the pyrido-indole moiety), wherein ring a 1 And ring A 2 Condensed with a pyrrolyl group.
Because the heterocyclic compound represented by formula 1 includes a condensed heterocyclic nucleus (wherein ring A 1 And ring A 2 Condensed with the pyrrolyl group), so that the bond dissociation energy is taken into account(BDE), the molecules may be more rigid, thus thermally stable and suitable for transferring energy.
In some embodiments, the heterocyclic compound represented by formula 1 may include at least one silol group, thereby improving electron injection and transport characteristics, and thus improving (increasing) light emission efficiency and lifetime characteristics of the light emitting device.
Therefore, a light emitting device, for example, an organic light emitting device, using the heterocyclic compound represented by formula 1 may have a low driving voltage, a high maximum quantum yield, a high light emitting efficiency, and a long lifetime.
Methods of synthesizing the heterocyclic compounds represented by formula 1 should be apparent to one of ordinary skill in the art by reference to the examples described herein.
At least one heterocyclic compound represented by formula 1 may be used in a light-emitting device (e.g., an organic light-emitting device).
Another aspect of embodiments of the present disclosure relates to a light emitting device, including: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and comprising an emissive layer; and at least one heterocyclic compound represented by formula 1.
In an embodiment, the first electrode may be an anode,
the second electrode may be a cathode electrode,
the interlayer may further include a hole transport region between the emissive layer and the first electrode, and the interlayer may further include an electron transport region between the emissive layer and the second electrode,
the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or one or more combinations thereof, and
the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or one or more combinations thereof.
In an embodiment, the emission layer may include at least one heterocyclic compound represented by formula 1.
In an embodiment, the emission layer may further include a transition metal-containing compound.
In an embodiment, the emission layer may emit blue light or blue-green light.
In an embodiment, the emission layer may emit blue light or blue-green light having a maximum emission wavelength ranging from about 400nm to about 500 nm.
As used herein, the expression "(interlayer) comprising a heterocyclic compound represented by formula 1" may be interpreted to mean "(interlayer) may comprise one heterocyclic compound represented by formula 1 or at least two different heterocyclic compounds represented by formula 1).
In an embodiment, the interlayer may include only compound 1 as the heterocyclic compound represented by formula 1. In this regard, the compound 1 may be present in an emission layer of a light emitting device. In one or more embodiments, the interlayer may include compound 1 and compound 2 as the heterocyclic compound represented by formula 1. In this regard, compound 1 and compound 2 may be present in substantially the same layer (e.g., all of compound 1 and compound 2 may be present in the emissive layer) or may be present in different layers (e.g., compound 1 may be present in the emissive layer and compound 2 may be present in the electron transport region).
As used herein, the term "interlayer" refers to a single layer and/or all of the multiple layers located between a first electrode and a second electrode of a light emitting device.
Another aspect of embodiments of the present disclosure relates to an electronic device including a light emitting apparatus. The electronic device may further include a thin film transistor.
For example, the electronic device may further include: a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode.
In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or one or more combinations thereof. For example, the electronic device may be a flat panel display device, but embodiments of the present disclosure are not limited thereto.
For more details on the electronic device, reference may be made to the relevant description provided herein.
Description of FIG. 1
Fig. 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.
Hereinafter, a structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to an embodiment will be described with reference to fig. 1.
First electrode 110
In fig. 1, the substrate may be additionally located under the first electrode 110 or on the second electrode 150. As the substrate, a glass substrate and/or a plastic substrate can be used. In one or more embodiments, the substrate may be a flexible substrate, and may include a plastic having excellent or suitable heat resistance and durability, such as Polyimide (PI), polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyaromatic ester (PAR), polyetherimide, or one or more combinations thereof.
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material used to form the first electrode 110 may be a high work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) 2 ) Zinc oxide (ZnO) or one or more combinations thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or one or more combinations thereof.
The first electrode 110 may have a single-layer structure including a single layer (e.g., composed of a single layer) or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
Interlayer 130
The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emissive layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
In addition to one or more suitable organic materials, interlayer 130 may further include metal-containing compounds such as organometallic compounds and/or inorganic materials such as quantum dots, and the like.
In one or more embodiments, the interlayer 130 may include: i) Two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emission units. When the interlayer 130 includes an emission unit and a charge generation layer as described above, the light emitting device 10 may be a tandem light emitting device.
Hole transport region in interlayer 130
The hole transport region may have: i) A single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a single material, ii) a single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a plurality of different materials, or iii) a multi-layer structure comprising a plurality of layers comprising (e.g., consisting of) a plurality of different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or one or more combinations thereof.
For example, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, and layers of the respective structures are stacked in order from the first electrode 110.
The hole transport region may include a compound represented by formula 201, a compound represented by formula 202, or any combination thereof:
201, a method for manufacturing a semiconductor device
Figure BDA0003941374030000241
202, respectively
Figure BDA0003941374030000242
Wherein, in the formulas 201 and 202,
L 201 to L 204 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
L 205 can be-O ', -S', -N (Q) 201 ) Unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xa1 to xa4 may each independently be an integer selected from 0 to 5,
xa5 may be an integer selected from 1 to 10,
R 201 to R 204 And Q 201 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
R 201 and R is 202 Optionally via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 Alkenylenes are linked to each other to form an unsubstituted or substituted radical with at least one R 10a Substituted C 8 -C 60 Polycyclic groups (e.g., carbazolyl groups, etc.) (e.g., compound HT 16),
R 203 And R is 204 Optionally via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted by at least one R 10a Substituted C 2 -C 5 Alkenylenes are linked to each other to form an unsubstituted or substituted radical with at least one R 10a Substituted C 8 -C 60 A polycyclic group, and
na1 may be an integer selected from 1 to 4.
For example, each of formulas 201 and 202 may include at least one of the groups represented by formulas CY201 to CY 217:
Figure BDA0003941374030000251
r in formulas CY201 to CY217 10b And R is 10c Each is with R 10a Is the same as the description of Cy 201 To ring CY 204 Can each independently be C 3 -C 20 Carbocyclyl or C 1 -C 20 Heterocyclyl, and at least one hydrogen of formulae CY201 to CY217 may be unsubstituted or substituted by R 10a And (3) substitution.
In one or more embodiments, the ring CY in formulas CY201 through CY217 201 To ring CY 204 And each independently may be phenyl, naphthyl, phenanthryl or anthracyl.
In one or more embodiments, each of formulas 201 and 202 may include at least one of the groups represented by formulas CY201 through CY 203.
In one or more embodiments, formula 201 may include at least one of the groups represented by formulas CY201 through CY203 and at least one of the groups represented by formulas CY204 through CY 217.
In one or more embodiments, xa1 in formula 201 may be 1, r 201 May be a group represented by one of the formulas CY201 to CY203, xa2 may be 0, and R 202 Can be one of the formulas CY204 to CY207And the radicals represented.
In one or more embodiments, each of formulas 201 and 202 may not include (e.g., may exclude) a group represented by one of formulas CY201 to CY 203.
In one or more embodiments, each of formulas 201 and 202 may not include (e.g., may exclude) a group represented by one of formulas CY201 to CY203, and may include at least one of groups represented by formulas CY204 to CY 217.
In one or more embodiments, each of formulas 201 and 202 may not include (e.g., may exclude) a group represented by one of formulas CY201 to CY 217.
For example, the hole transport layer may include one of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), 1, 3-bis (9-carbazolyl) benzene (mCP), β -NPB, TPD, spirotpd, spironpb, methylated NPB, TAPC, HMTPD, 4',4″ -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/PSS), or one or more combinations thereof:
Figure BDA0003941374030000271
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Figure BDA0003941374030000281
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Figure BDA0003941374030000291
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Figure BDA0003941374030000301
Figure BDA0003941374030000311
/>
The hole transport region may have a thickness of about
Figure BDA0003941374030000312
To about->
Figure BDA0003941374030000313
For example, about->
Figure BDA0003941374030000314
To about->
Figure BDA0003941374030000315
Within a range of (2). When the hole transport region comprises a hole injection layer, a hole transport layer, or any combination thereof, the hole injection layer may have a thickness of about +.>
Figure BDA0003941374030000316
To about->
Figure BDA0003941374030000317
For example, about->
Figure BDA0003941374030000318
To about->
Figure BDA0003941374030000319
Within a range of (2), and the thickness of the hole transport layer may be about +.>
Figure BDA00039413740300003110
To about->
Figure BDA00039413740300003111
For example, about->
Figure BDA00039413740300003112
To about->
Figure BDA00039413740300003113
Is of (2)And is enclosed inside. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory (appropriate) hole transport characteristics can be obtained without significantly increasing the driving voltage.
The emission assisting layer may increase luminous efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce a flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer may comprise materials as described above.
P-dopant
In addition to these materials, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generating material).
The charge generating material may be, for example, a p-dopant.
For example, the Lowest Unoccupied Molecular Orbital (LUMO) level of the p-dopant may be-3.5 eV or less.
In one or more embodiments, the p-dopant can include a quinone derivative, a cyano-containing compound, a compound comprising element EL1 and element EL2, or one or more combinations thereof.
Examples of quinone derivatives are TCNQ, F4-TCNQ, and the like.
Examples of the cyano group-containing compound are HAT-CN and a compound represented by formula 221:
Figure BDA0003941374030000321
221 of a pair of rollers
Figure BDA0003941374030000322
In the process of 221,
R 221 to R 223 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl group, and
R 221 to R 223 At least one of which may each independently be C, each substituted with 3 -C 60 Carbocyclyl or C 1 -C 60 A heterocyclic group: cyano group; -F; -Cl; -Br; -I; c substituted with cyano, -F, -Cl, -Br, -I, or any combination thereof 1 -C 20 An alkyl group; or one or more combinations thereof.
In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or one or more combinations thereof, and the element EL2 may be a nonmetal, a metalloid, or one or more combinations thereof.
Examples of the metal are alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.; post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and/or lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of metalloids are silicon (Si), antimony (Sb) and/or tellurium (Te).
Examples of non-metals are oxygen (O) and/or halogen (e.g., F, cl, br, I, etc.).
Examples of compounds that include element EL1 and element EL2 are metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or one or more combinations thereof.
Representation of metal oxidesExamples are tungsten oxides (e.g. WO, W 2 O 3 、WO 2 、WO 3 、W 2 O 5 Etc.), vanadium oxides (e.g., VO, V 2 O 3 、VO 2 、V 2 O 5 Etc.), molybdenum oxide (MoO, mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 Etc.) and/or rhenium oxide (e.g., reO 3 Etc.).
Examples of metal halides are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides and/or lanthanide metal halides.
Examples of alkali halides are LiF, naF, KF, rbF, csF, liCl, naCl, KCl, rbCl, csCl, liBr, naBr, KBr, rbBr, csBr, liI, naI, KI, rbI and CsI.
An example of an alkaline earth metal halide is BeF 2 、MgF 2 、CaF 2 、SrF 2 、BaF 2 、BeCl 2 、MgCl 2 、CaCl 2 、SrCl 2 、BaCl 2 、BeBr 2 、MgBr 2 、CaBr 2 、SrBr 2 、BaBr 2 、BeI 2 、MgI 2 、CaI 2 、SrI 2 And/or BaI 2 。
Examples of transition metal halides are titanium halides (e.g., tiF 4 、TiCl 4 、TiBr 4 、TiI 4 Etc.), zirconium halides (e.g., zrF 4 、ZrCl 4 、ZrBr 4 、ZrI 4 Etc.), hafnium halides (e.g., hfF 4 、HfCl 4 、HfBr 4 、HfI 4 Etc.), vanadium halides (e.g., VF 3 、VCl 3 、VBr 3 、VI 3 Etc.), niobium halides (e.g., nbF 3 、NbCl 3 、NbBr 3 、NbI 3 Etc.), tantalum halides (e.g., taF 3 、TaCl 3 、TaBr 3 、TaI 3 Etc.), chromium halides (e.g., crF 3 、CrCl 3 、CrBr 3 、CrI 3 Etc.), molybdenum halides (e.g., moF 3 、MoCl 3 、MoBr 3 、MoI 3 Etc.), tungsten halides (e.g., WF 3 、WCl 3 、WBr 3 、WI 3 Etc.), manganese halides (e.g., mnF 2 、MnCl 2 、MnBr 2 、MnI 2 Etc.), technetium halides (e.g., tcF 2 、TcCl 2 、TcBr 2 、TcI 2 Etc.), rhenium halides (e.g., ref 2 、ReCl 2 、ReBr 2 、ReI 2 Etc.), iron halides (e.g., feF 2 、FeCl 2 、FeBr 2 、FeI 2 Etc.), ruthenium halides (e.g., ruF 2 、RuCl 2 、RuBr 2 、RuI 2 Etc.), osmium halides (e.g., osF 2 、OsCl 2 、OsBr 2 、OsI 2 Etc.), cobalt halides (e.g., coF 2 、CoCl 2 、CoBr 2 、CoI 2 Etc.), rhodium halides (e.g., rhF 2 、RhCl 2 、RhBr 2 、RhI 2 Etc.), iridium halides (e.g., irF 2 、IrCl 2 、IrBr 2 、IrI 2 Etc.), nickel halides (e.g., niF 2 、NiCl 2 、NiBr 2 、NiI 2 Etc.), palladium halides (e.g., pdF 2 、PdCl 2 、PdBr 2 、PdI 2 Etc.), platinum halides (e.g., ptF 2 、PtCl 2 、PtBr 2 、PtI 2 Etc.), copper halides (e.g., cuF, cuCl, cuBr, cuI, etc.), silver halides (e.g., agF, agCl, agBr, agI, etc.), and/or gold halides (e.g., auF, auCl, auBr, auI, etc.).
Examples of late transition metal halides are zinc halides (e.g., znF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 Etc.), indium halides (e.g., inI 3 Etc.) and/or tin halides (e.g., snI 2 Etc.).
Examples of lanthanide metal halides are YbF, ybF 2 、YbF 3 、SmF 3 、YbCl、YbCl 2 、YbCl 3 SmCl 3 、YbBr、YbBr 2 、YbBr 3 、SmBr 3 、YbI、YbI 2 、YbI 3 And/or Smi 3 。
Examples of metalloid halides are antimony halides (e.g., sbCl 5 Etc.).
Examples of metal telluride are alkali metal telluride (e.g., li 2 Te、Na 2 Te、K 2 Te、Rb 2 Te、Cs 2 Te, etc.), alkaline earth metal telluride (e.g., beTe, mgTe, caTe, srTe, baTe, etc.), transition metal telluride (e.g., tiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 、Nb 2 Te 3 、Ta 2 Te 3 、Cr 2 Te 3 、Mo 2 Te 3 、W 2 Te 3 、MnTe、TcTe、ReTe、FeTe、RuTe、OsTe、CoTe、RhTe、IrTe、NiTe、PdTe、PtTe、Cu 2 Te、CuTe、Ag 2 Te、AgTe、Au 2 Te, etc.), late transition metal telluride (e.g., znTe, etc.), and/or lanthanide metal telluride (e.g., laTe, ceTe, prTe, ndTe, pmTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, etc.).
Emissive layer in interlayer 130
When the light emitting device 10 is a full color light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer according to the subpixels. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light. In one or more embodiments, the emission layer may include two or more materials of a red light emitting material, a green light emitting material, and a blue light emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
The emissive layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
The host may include at least one heterocyclic compound represented by formula 1.
The amount of dopant in the emissive layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
In one or more embodiments, the emissive layer may include quantum dots.
In some embodiments, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or dopant in the emissive layer.
The thickness of the emissive layer may be about
Figure BDA0003941374030000341
To about->
Figure BDA0003941374030000342
For example, about->
Figure BDA0003941374030000343
To about->
Figure BDA0003941374030000344
Within a range of (2). When the thickness of the emission layer is within these ranges, excellent or appropriate light emission characteristics can be obtained without significantly increasing the driving voltage.
Main body
The host may include at least one heterocyclic compound represented by formula 1.
The host may further include a compound represented by formula 301:
301
[Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ，
In the formula (301) of the present invention,
Ar 301 and L 301 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xb11 may be 1, 2 or 3,
xb1 may be an integer selected from 0 to 5,
R 301 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl and cyanogenRadicals, nitro radicals, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, -Si (Q) 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(＝O)(Q 301 )、-S(＝O) 2 (Q 301 ) or-P (=O) (Q 301 )(Q 302 )，
xb21 may be an integer selected from 1 to 5, and
Q 301 to Q 303 Each is with Q 1 The description of (2) is the same.
For example, when xb11 in formula 301 is 2 or more, two or more Ar 301 Can be connected to each other via a single bond.
In one or more embodiments, the host may include a compound represented by formula 301-1, a compound represented by formula 301-2, or one or more combinations thereof:
301-1
Figure BDA0003941374030000351
301-2
Figure BDA0003941374030000352
Wherein, in the formulas 301-1 and 301-2,
ring A 301 To ring A 304 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
X 301 can be O, S, N [ (L) 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) Or Si (R) 304 )(R 305 )，
xb22 and xb23 may each independently be 0, 1 or 2,
L 301 xb1 and R 301 Can be respectively with L described herein 301 Xb1 and R 301 The same is true of the fact that,
L 302 to L 304 Can be independently from each other L 301 The description of (c) is the same,
xb2 to xb4 can each independently be the same as the description of xb1, and
R 302 to R 305 And R is 311 To R 314 Can be respectively with R 301 The description of (2) is the same.
In one embodiment, the body may include an alkaline earth metal complex. For example, the host may include Be complexes (e.g., compound H55), mg complexes, zn complexes, or one or more combinations thereof.
In one or more embodiments, the host may include one of compounds H1 through H124, 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), 9, 10-bis (2-naphthyl) -2-tert-butyl-anthracene (TBADN), 4 '-bis (N-carbazolyl) -1,1' -biphenyl (CBP), 1, 3-bis (9-carbazolyl) benzene (mCP), 3 '-bis (9H-carbazol-9-yl) -1,1' -biphenyl (mCBP), 1,3, 5-tris (carbazol-9-yl) benzene (TCP), bis (4- (9H-carbazol-9-yl) phenyl) diphenylsilane (BCPDS), DPEPO, or one or more combinations thereof.
Figure BDA0003941374030000361
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Figure BDA0003941374030000371
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Figure BDA0003941374030000381
/>
Figure BDA0003941374030000391
/>
Figure BDA0003941374030000401
/>
Figure BDA0003941374030000411
/>
Figure BDA0003941374030000421
Figure BDA0003941374030000431
Phosphorescent dopants
In one or more embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.
Phosphorescent dopants may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
Phosphorescent dopants may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by formula 401:
401
M(L 401 ) xc1 (L 402 ) xc2 ，
Wherein, in the formula 401,
m may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
L 401 may be a ligand represented by formula 402, and xc1 may be 1, 2, or 3, wherein when xc1 is 2 or more, two or more L 401 May be the same as or different from each other,
L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, and when xc2 is 2 or more, two or more L 402 May be the same as or different from each other,
402 of the following kind
Figure BDA0003941374030000432
In formula 402, X 401 And X 402 Each of which may independently be nitrogen or carbon,
ring A 401 And ring A 402 Can each independently be C 3 -C 60 Carbocyclyl or C 1 -C 60 A heterocyclic group,
T 401 can be single bond, —o ', -S', -C (=o) -, -N (Q) 411 )-*’、*-C(Q 411 )(Q 412 )-*’、
*-C(Q 411 )＝C(Q 412 )-*’、*-C(Q 411 ) Either = 'or = C =',
X 403 and X 404 Can each independently be a chemical bond (e.g., covalent or coordinate), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) Or Si (Q) 413 )(Q 414 )，
Q 411 To Q 414 Can be respectively with Q 1 The description of (c) is the same,
R 401 and R is 402 Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstitutedOr by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, -Si (Q) 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(＝O)(Q 401 )、-S(＝O) 2 (Q 401 ) or-P (=O) (Q 401 )(Q 402 )，
Q 401 To Q 403 Can be respectively with Q 1 The description of (c) is the same,
xc11 and xc12 may each independently be an integer selected from 0 to 10, and
each of the formulae 402 and' indicates a bonding site to M in formula 401.
For example, in formula 402, i) X 401 Can be nitrogen, and X 402 Can be carbon, or ii) X 401 And X 402 May be nitrogen.
In one or more embodiments, when xc1 in formula 401 is 2 or greater, two or more L 401 Two rings A in (a) 401 Optionally via T as a linking group 402 Are connected to each other and two rings A 402 Optionally via T as a linking group 403 Are linked to each other (see compound PD1 to compound PD4 and compound PD 7). T (T) 402 And T 403 Each is associated with T 401 The description of (2) is the same.
L in formula 401 402 May be an organic ligand. For example, L 402 May include halo, diketo (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), C (=o), isonitrile, -CN, phosphorus-containing (e.g., phosphine, phosphite, etc.), or one or more combinations thereof.
Phosphorescent dopants may include, for example, one of compounds PD1 to PD39 or one or more combinations thereof:
Figure BDA0003941374030000451
/>
Figure BDA0003941374030000461
/>
Figure BDA0003941374030000471
Fluorescent dopants
The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or one or more combinations thereof.
For example, the fluorescent dopant may include a compound represented by formula 501:
501, a method of manufacturing a semiconductor device
Figure BDA0003941374030000472
Wherein, in the formula 501,
Ar 501 、L 501 to L 503 、R 501 And R is 502 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xd1 to xd3 can each independently be 0, 1,2 or 3, and
xd4 may be 1,2, 3, 4, 5 or 6.
For example, ar in formula 501 501 May be a fused ring group (e.g., anthracenyl, 1, 2-benzophenanthryl or pyrenyl) in which three or more monocyclic groups are fused together.
In one or more embodiments, xd4 in equation 501 can be 2.
For example, the fluorescent dopant may include: one of the compounds FD1 to FD 36; DPVBi; DPAVBi; or one or more combinations thereof:
Figure BDA0003941374030000481
/>
Figure BDA0003941374030000491
/>
Figure BDA0003941374030000501
delayed fluorescent material
The emissive layer may include a delayed fluorescent material.
In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescent material included in the emission layer may act as a host or dopant depending on the type or kind of other materials included in the emission layer.
In one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be greater than or equal to 0eV and less than or equal to 0.5eV. When the difference between the triplet level (eV) of the delayed fluorescent material and the singlet level (eV) of the delayed fluorescent material satisfies the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state can effectively occur, and thus, the light emitting efficiency of the light emitting device 10 can be improved (increased).
For example, the delayed fluorescent material may include: i) Comprising at least one electron donor (e.g. pi-electron rich C 3 -C 60 Cyclic groups, such as carbazolyl groups), and at least one electron acceptor (e.g., sulfoxide groups, cyano groups, or pi-electron deficient nitrogen-containing C 1 -C 60 Cyclic groups), and ii) a material comprising C wherein two or more cyclic groups are fused while sharing boron (B) 8 -C 60 Materials with polycyclic groups.
Examples of the delayed fluorescent material may include at least one of the following compounds DF1 to DF 9:
Figure BDA0003941374030000511
quantum dot
The emissive layer may comprise quantum dots.
As used herein, the term "quantum dot" refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more appropriate emission wavelengths depending on the size of the crystal.
The diameter of the quantum dots may be, for example, in the range of about 1nm to about 10 nm.
The quantum dots may be synthesized by wet chemical processes, metal Organic Chemical Vapor Deposition (MOCVD) processes, molecular Beam Epitaxy (MBE) processes, or any similar (suitable) processes thereto, which should be apparent to one of ordinary skill in the art upon reading this disclosure.
Wet chemical processes are methods that include mixing a precursor material with an organic solvent and then growing the quantum dot particle crystals. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal, and controls the growth of the crystal so that the growth of the quantum dot particles can be controlled or selected by a process which is lower in cost and easier than a vapor deposition method such as a metal organic chemical vapor deposition process or a molecular beam epitaxy process.
The quantum dots may include group III-VI semiconductor compounds; group II-VI semiconductor compounds; a group III-V semiconductor compound; group III-VI semiconductor compounds; a group I-III-VI semiconductor compound; group IV-VI semiconductor compounds; group IV elements or compounds; or one or more combinations thereof.
Examples of the group III-VI semiconductor compound may include: binary compounds, e.g. In 2 S 3 The method comprises the steps of carrying out a first treatment on the surface of the Ternary compounds, e.g. AgInS, agInS 2 CuInS or CuInS 2 The method comprises the steps of carrying out a first treatment on the surface of the Or one or more combinations thereof.
Examples of the group II-VI semiconductor compound may be a binary compound such as CdSe, cdTe, znS, znSe, znTe, znO, hgS, hgSe, hgTe, mgSe or MgS; ternary compounds such as CdSeS, cdSeTe, cdSTe, znSeS, znSeTe, znSTe, hgSeS, hgSeTe, hgSTe, cdZnS, cdZnSe, cdZnTe, cdHgS, cdHgSe, cdHgTe, hgZnS, hgZnSe, hgZnTe, mgZnSe or MgZnS; quaternary compounds such as CdZnSeS, cdZnSeTe, cdZnSTe, cdHgSeS, cdHgSeTe, cdHgSTe, hgZnSeS, hgZnSeTe or HgZnSTe; or one or more combinations thereof.
Examples of the group III-V semiconductor compound may be binary compounds such as GaN, gaP, gaAs, gaSb, alN, alP, alAs, alSb, inN, inP, inAs and/or InSb, etc.; ternary compounds such as GaNP, gaNAs, gaNSb, gaPAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inGaP, inNP, inAlP, inNAs, inNSb, inPAs and/or InPSb, etc.; quaternary compounds such as GaAlNP, gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gaInNP, gaInNAs, gaInNSb, gaInPAs, gaInPSb, inAlNP, inAlNAs, inAlNSb, inAlPAs and/or InAlPSb, etc.; or one or more combinations thereof. In some embodiments, the group III-V semiconductor compound may further include a group II element. An example of a group III-V semiconductor compound further including a group II element is InZnP, inGaZnP, inAlZnP and the like.
Examples of the group III-VI semiconductor compounds may be: binary compounds, e.g. GaS, gaSe, ga 2 Se 3 、GaTe、InS、InSe、In 2 Se 3 Or InTe; ternary compounds, e.g. InGaS 3 Or InGaSe 3 The method comprises the steps of carrying out a first treatment on the surface of the Or one or more combinations thereof.
Examples of the group I-III-VI semiconductor compound may be: ternary compounds, e.g. AgInS, agInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 Or AgAlO 2 The method comprises the steps of carrying out a first treatment on the surface of the Or one or more combinations thereof.
Examples of group IV-VI semiconductor compounds may be: binary compounds such as SnS, snSe, snTe, pbS, pbSe or PbTe; ternary compounds such as SnSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe or SnPbTe; quaternary compounds such as SnPbSSe, snPbSeTe or SnPbSTe; or one or more combinations thereof.
The group IV element or compound may include: single elements such as Si or Ge; binary compounds such as SiC or SiGe; or one or more combinations thereof.
Each element included in the multi-component compounds such as binary, ternary, and quaternary compounds may be present in the particulate form in a substantially uniform concentration or in a non-uniform concentration.
In some embodiments, the quantum dots may have a single structure in which the concentration of each element in the quantum dots is substantially uniform, or a core/shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer to prevent chemical denaturation of the core to preserve semiconductor characteristics, and/or as a charge layer to impart electrophoretic characteristics to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.
Examples of shells of quantum dots may be oxides of metals or non-metals, semiconductor compounds, and one or more combinations thereof. Examples of oxides of metals or non-metals may be binary compounds, such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 、Mn 3 O 4 、CuO、FeO、Fe 2 O 3 、Fe 3 O 4 、CoO、Co 3 O 4 Or NiO; ternary compounds, e.g. MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 Or CoMn 2 O 4 The method comprises the steps of carrying out a first treatment on the surface of the And one or more combinations thereof. Examples of semiconductor compounds may be group III-VI semiconductor compounds as described herein; group II-VI semiconductor compounds; a group III-V semiconductor compound; group III-VI semiconductor compounds; a group I-III-VI semiconductor compound; group IV-VI semiconductor compounds; and one or more combinations thereof. For example, the semiconductor compound may include CdS, cdSe, cdTe, znS, znSe, znTe, znSeS, znTeS, gaAs, gaP, gaSb, hgS, hgSe, hgTe, inAs, inP, inGaP, inSb, alAs, alP, alSb or one or more combinations thereof.
The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be about 45nm or less, for example, about 40nm or less, for example, about 30nm or less, and in these ranges, color purity and/or color reproducibility may be increased. In some embodiments, since light emitted by the quantum dots is emitted in all directions, a wide viewing angle may be improved (increased).
In some embodiments, the quantum dots may be in the form of substantially spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
Since the energy bandgap can be adjusted by controlling the size of the quantum dots, light having one or more appropriate wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by utilizing quantum dots of different sizes, a light emitting device that emits light of one or more appropriate wavelengths may be implemented. In one or more embodiments, the size of the quantum dots can be selected to emit red, green, and/or blue light. In some embodiments, the size of the quantum dots may be configured to emit white light by combining light of one or more appropriate colors.
Electron transport regions in interlayer 130
The electron transport region may have: i) A single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a single material, ii) a single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a plurality of different materials, or iii) a multi-layer structure comprising a plurality of layers comprising (e.g., consisting of) a plurality of different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or one or more combinations thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, the constituent layers of each structure being stacked in order from the emission layer.
In embodiments, the electron transport region (e.g., buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may comprise a metal-free compound comprising at least one pi electron deficient nitrogen-containing C 1 -C 60 A cyclic group.
For example, the electron transport region may include a compound represented by formula 601:
601 and method for manufacturing the same
[Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ，
Wherein, in the formula 601,
Ar 601 and L 601 Can each independently be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
xe11 may be 1, 2 or 3,
xe1 may be 0, 1, 2, 3, 4 or 5,
R 601 can be unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, -Si (Q) 601 )(Q 602 )(Q 603 )、-C(＝O)(Q 601 )、-S(＝O) 2 (Q 601 ) or-P (=O) (Q 601 )(Q 602 )，
Q 601 To Q 603 Can be respectively with Q 1 Is the same as the description of
xe21 may be 1, 2, 3, 4 or 5,
Ar 601 、L 601 and R is 601 At least one of which may each independently be unsubstituted or substituted with at least one R 10a Substituted pi electron deficient nitrogen containing C 1 -C 60 A cyclic group.
For example, when xe11 in formula 601 is 2 or more, two or more Ar 601 Can be connected to each other by single bond。
In other embodiments, ar in formula 601 601 May be substituted or unsubstituted anthracyl.
In other embodiments, the electron transport region may include a compound represented by formula 601-1:
601-1
Figure BDA0003941374030000551
Wherein, in the formula 601-1,
X 614 can be N or C (R) 614 )，X 615 Can be N or C (R) 615 )，X 616 Can be N or C (R) 616 ) And X is 614 To X 616 At least one of which may be N,
L 611 to L 613 Can be respectively with L 601 The description of (c) is the same,
xe611 to xe613 may each be the same as the description of xe1,
R 611 to R 613 Can be each with R 601 Is the same as described in (a), and
R 614 to R 616 Can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group.
For example, xe1 and xe611 to xe613 in formula 601 and formula 601-1 may each be independently 0, 1 or 2.
The electron transport region may include one of the compounds ET1 to ET45, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), diphenyl (4- (triphenylsilyl) phenyl) -phosphine oxide (TSPO 1), alq 3 BAlq, TAZ, NTAZ, DPEPO, or one or more combinations thereof:
Figure BDA0003941374030000552
/>
Figure BDA0003941374030000561
/>
Figure BDA0003941374030000571
/>
Figure BDA0003941374030000581
the electron transport region may have a thickness of about
Figure BDA0003941374030000582
To about->
Figure BDA0003941374030000583
For example, about->
Figure BDA0003941374030000584
To about->
Figure BDA0003941374030000585
When the electron transport region comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or one or more combinations thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be about->
Figure BDA0003941374030000586
To about->
Figure BDA0003941374030000587
For example, about->
Figure BDA0003941374030000588
To about->
Figure BDA0003941374030000589
And the thickness of the electron transport layer may be about +. >
Figure BDA00039413740300005810
To about->
Figure BDA00039413740300005811
For example, about->
Figure BDA00039413740300005812
To about->
Figure BDA00039413740300005813
When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory (appropriate) electron transport characteristics can be obtained without significantly increasing the driving voltage.
In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further comprise a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The metal ion of the alkali metal complex may Be Li ion, na ion, K ion, rb ion or Cs ion, and the metal ion of the alkaline earth metal complex may Be ion, mg ion, ca ion, sr ion or Ba ion. The ligand that coordinates to the metal ion of the alkali metal complex or alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination of one or more thereof.
For example, the metal-containing material may include a Li complex. Li complexes may include, for example, compound ET-D1 (Liq) or compound ET-D2:
Figure BDA0003941374030000591
the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have: i) A single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a single material, ii) a single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a plurality of different materials, or iii) a multi-layer structure comprising a plurality of layers comprising (e.g., consisting of) a plurality of different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or one or more combinations thereof.
The alkali metal may comprise Li, na, K, rb, cs or one or more combinations thereof. The alkaline earth metal may comprise Mg, ca, sr, ba or one or more combinations thereof. The rare earth metal may comprise Sc, Y, ce, tb, yb, gd or one or more combinations thereof.
The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound may be an oxide, halide (e.g., fluoride, chloride, bromide, or iodide) or telluride of an alkali metal, alkaline earth metal, and/or rare earth metal, or one or more combinations thereof.
The alkali metal-containing compound may include: alkali metal oxides, e.g. Li 2 O、Cs 2 O or K 2 O; alkali metal halides, such as LiF, naF, csF, KF, liI, naI, csI or KI; or one or more combinations thereof. The alkaline earth metal-containing compound may include an alkaline earth metal oxide, such as BaO, srO, caO, ba x Sr 1-x O (wherein x is 0<x<A real number of the condition of 1) and/or Ba x Ca 1-x O (wherein x is 0<x<A real number of the condition of 1), and the like. The rare earth-containing metal compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 Or one or more combinations thereof. In one or more embodiments, the rare earth-containing compound may include a lanthanide metal telluride. An example of a lanthanide metal telluride may be LaTe, ceTe, prTe, ndTe, pmTe, smTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, la 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 、Gd 2 Te 3 、Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 、Er 2 Te 3 、Tm 2 Te 3 、Yb 2 Te 3 And/or Lu 2 Te 3 。
The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include: i) One or more of the metal ions of alkali metals, alkaline earth metals and/or rare earth metals, and ii) a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or one or more combinations thereof.
The electron injection layer may include (e.g., consist of) the following: the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or one or more combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by formula 601).
In one or more embodiments, the electron injection layer can include (e.g., consist of) the following: i) Alkali metal-containing compounds (e.g., alkali metal halides); or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide), and b) an alkali metal, alkaline earth metal, rare earth metal, or one or more combinations thereof. For example, the electron injection layer may be a KI: yb co-deposited layer and/or a RbI: yb co-deposited layer, etc.
When the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or one or more combinations thereof may be substantially uniformly or non-uniformly dispersed in a matrix comprising the organic material.
The electron injection layer may have a thickness of about
Figure BDA0003941374030000601
To about->
Figure BDA0003941374030000602
For example, about->
Figure BDA0003941374030000603
To about->
Figure BDA0003941374030000604
Within a range of (2). When the thickness of the electron injection layer is within the above-described range, satisfactory (appropriate) electron injection characteristics can be obtained without significantly increasing the driving voltage.
Second electrode 150
The second electrode 150 may be positioned on the interlayer 130 having the structure as described above. The second electrode 150 may be a cathode as an electron injection electrode, and metals, alloys, conductive compounds each having a low work function, or one or more combinations thereof may be used as a material for the second electrode 150.
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or one or more combinations thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
Capping layer
The first capping layer may be located outside the first electrode 110 and/or the second capping layer may be located outside the second electrode 150. In particular, the light emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in the emission layer of the interlayer 130 of the light emitting device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer. Light generated in the emission layer of the interlayer 130 of the light emitting device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to principles of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index (at 589 nm) of 1.6 or more.
The first capping layer and the second capping layer may each be independently an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer and the second capping layer may each independently comprise a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination of one or more thereof. Optionally, the carbocyclic compound, heterocyclic compound, and amine-containing compound may be substituted with substituents including O, N, S, se, si, F, cl, br, I or one or more combinations thereof. In one or more embodiments, at least one of the first capping layer and the second capping layer may each independently include an amine-containing compound.
For example, at least one of the first capping layer and the second capping layer may each independently include a compound represented by formula 201, a compound represented by formula 202, or one or more combinations thereof.
In one or more embodiments, at least one of the first capping layer and the second capping layer may each independently comprise one of compounds HT28 to HT33, one of compounds CP1 to CP6, β -NPB, or one or more combinations thereof:
Figure BDA0003941374030000621
electronic equipment
The light emitting means may be comprised in one or more suitable electronic devices. For example, the electronic device comprising the light emitting means may be a light emitting device and/or an authentication device or the like.
In addition to the light emitting apparatus, the electronic device (e.g., light emitting device) may further include: i) A color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be located in at least one traveling direction of light emitted from the light emitting device. For example, the light emitted from the light emitting device may be blue light or white light. For more details on the light emitting device, reference is made to the relevant description provided above. In one or more embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.
The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.
The pixel defining layer may be located between the plurality of sub-pixel regions to define each of the plurality of sub-pixel regions.
The color filter may further include a plurality of color filter regions and a light shielding pattern between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern between the plurality of color conversion regions.
The plurality of color filter regions (or the plurality of color conversion regions) may include a first region that emits first color light, a second region that emits second color light, and/or a third region that emits third color light, wherein the first color light, the second color light, and/or the third color light may have maximum emission wavelengths different from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. For example, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include (e.g., may exclude) quantum dots. For more details regarding quantum dots, reference may be made to the relevant descriptions provided herein. The first region, the second region and/or the third region may each comprise a diffuser.
For example, the light emitting device may emit first light, the first region may absorb the first light to emit first-first color light, the second region may absorb the first light to emit second-first color light, and the third region may absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
In addition to the light emitting device described above, the electronic apparatus may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode or the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light emitting device.
The thin film transistor may further include a gate electrode and/or a gate insulating film, or the like.
The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and/or an oxide semiconductor, etc.
The electronic apparatus may further include a sealing portion for sealing the light emitting device. The sealing portion may be located between the color conversion layer and/or the color filter and the light emitting device. The sealing portion allows light from the light emitting device to be extracted to the outside, and at the same time (e.g., concurrently) prevents (reduces) penetration of ambient air and moisture into the light emitting device. The sealing part may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
Depending on the use of the electronic device, various functional layers may be additionally located on the sealing portion in addition to the color filters and/or the color conversion layer. Examples of functional layers may include touch screen layers and/or polarizing layers, and the like. The touch screen layer may be a pressure sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., a fingertip, a pupil, etc.).
The authentication apparatus may further include a biometric information collector in addition to the light emitting device as described above.
The electronic device may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic gaming machines, medical tools (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscope displays), fish probes, one or more suitable measuring tools, meters (e.g., meters for vehicles, aircraft, and watercraft), and/or projectors, among others.
Description of fig. 2 and 3
Fig. 2 is a cross-sectional view showing a light emitting device according to an embodiment of the present disclosure.
The light emitting apparatus of fig. 2 includes a substrate 100, a Thin Film Transistor (TFT), a light emitting device, and a package portion 300 sealing the light emitting device.
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100, and may provide a flat surface on the substrate 100.
The TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and/or a drain electrode 270.
The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and/or a channel region.
A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be located on the active layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be positioned between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the source electrode 260, to insulate the gate electrode 240 from the drain electrode 270, and/or to insulate the source electrode 260 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be positioned on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source and drain regions of the active layer 220, and the source and drain electrodes 260 and 270 may be placed to contact the exposed portions of the source and drain regions of the active layer 220.
The TFT is electrically connected to the light emitting device to drive the light emitting device, and is covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or one or more combinations thereof. The light emitting device is provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and/or a second electrode 150.
The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may be placed such that it may expose a portion of the drain electrode 270, not entirely cover the drain electrode 270, and the first electrode 110 may be placed such that it may be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose certain regions of the first electrode 110, and the interlayer 130 may be formed in the exposed regions of the first electrode 110. The pixel defining layer 290 may be a polyimide or a polyacrylic acid organic film. At least some of the layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 while being disposed in the form of a common layer.
The second electrode 150 may be located on the interlayer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on the light emitting device to protect the light emitting device from moisture or oxygen. The encapsulation part 300 may include: inorganic films comprising silicon nitride (SiN) x ) Silicon oxide (SiO) x ) Indium tin oxide, indium zinc oxide, or one or more combinations thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyaromatic esters, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and/or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic Glycidyl Ethers (AGEs), etc.), or a combination of one or more thereof; or one or more combinations of inorganic and organic films.
Fig. 3 shows a cross-sectional view showing a light emitting device according to another embodiment of the present disclosure.
The light emitting device of fig. 3 is substantially the same as the light emitting device of fig. 2 except that the light shielding pattern 500 and the functional region 400 are additionally located on the encapsulation part 300. The functional area 400 may be: i) A color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. In an embodiment, the light emitting device included in the light emitting apparatus of fig. 3 may be a tandem light emitting device.
Method of manufacture
The layers constituting the hole transport region, the emissive layer, and the layers constituting the electron transport region may be formed in some regions by using one or more suitable methods such as vacuum deposition, spin coating, casting, langmuir-blodgett (LB) deposition, ink-jet printing, laser printing, and/or laser-induced thermal imaging, etc.
When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100 to about 500 c, about 10 -8 To about 10 -3 Vacuum level of the tray and the like
Figure BDA0003941374030000651
Per second to about
Figure BDA0003941374030000652
The deposition rate/sec, depending on the material to be included in the layer to be formed and/or the structure of the layer to be formed.
Definition of terms
As used herein, the term "C 3 -C 60 Carbocyclyl "refers to a cyclic group consisting of only carbon atoms and having 3 to 60 carbon atoms, and as used herein, the term" C 1 -C 60 A heterocyclic group "refers to a cyclic group having 1 to 60 carbon atoms and further having a heteroatom in addition to the carbon atoms. C (C) 3 -C 60 Carbocyclyl and C 1 -C 60 The heterocyclic groups may each be a monocyclic group including one ring (e.g., consisting of one ring) or a polycyclic group in which two or more rings are condensed with each other. For example, C 1 -C 60 The number of ring forming atoms of the heterocyclyl group may be 3 to 61.
As used herein, "cyclic group" may include C 3 -C 60 Carbocyclyl and C 1 -C 60 A heterocyclic group.
As used herein, the term "pi-electron rich C 3 -C 60 The cyclic group "refers to a cyclic group having 3 to 60 carbon atoms and excluding = -N' as a ring forming moiety, and as used herein, the term" pi electron deficient nitrogen-containing C 1 -C 60 The cyclic group "means having 1 to 60 carbon atoms and includes = -N =' asHeterocyclic groups that are cyclic moieties.
For example, the number of the cells to be processed,
C 3 -C 60 carbocyclyl can be i) a T1 group or ii) a fused ring group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentylene, naphthyl, azulenyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, perylenyl, pentylphenyl, heptenyl, tetracenyl, picenyl, hexaphenyl, pentacenyl, yuzuelanyl, coroneyl, egg phenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenofrenyl, or indenoanthrenyl),
C 1 -C 60 the heterocyclic group may be i) a T2 group, ii) a fused ring group in which at least two T2 groups are fused to each other, or iii) a fused ring group in which at least one T2 group and at least one T1 group are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphtalindolyl, isoindolyl, benzisoindolyl, naphtalindolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofurancarbazolyl, benzothiocarbazolyl, benzil carbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphtalenofuranyl, benzonaphtalenothienyl, benzonaphtalolyl, benzodibenzofuranyl, benzodibenzobenzothienyl, benzodibenzofuranyl, benzodibenzothiophenyl benzothiophenodibenzothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotritriazinyl Oxazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilol, azadibenzothienyl and/or azadibenzofuranyl, and the like),
pi electron rich C 3 -C 60 The cyclic group may be i) a T1 group, ii) a fused ring group in which two or more T1 groups are fused to each other, iii) a T3 group, iv) a fused ring group in which two or more T3 groups are fused to each other, or v) a fused ring group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C) 3 -C 60 Carbocyclyl, pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphtoindolyl, isoindolyl, benzisoindolyl, naphtalindolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzosilol, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphtofuranyl, benzonaphtalothienyl, benzonaphtalosilol, benzodibenzofuranyl, benzodibenzothiophenyl and/or benzothiophenal dibenzothiophenyl, etc.),
Pi electron deficient nitrogen containing C 1 -C 60 The cyclic group may be i) a T4 group, ii) a fused ring group in which two or more T4 groups are fused to each other, iii) a fused ring group in which at least one T4 group and at least one T1 group are fused to each other, iv) a fused ring group in which at least one T4 group and at least one T3 group are fused to each other, or v) a fused ring group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinoxalinyl, quinazolinyl, quinoxalinylBenzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilol, azadibenzothienyl, azadibenzofuranyl, and the like),
T1 groups may be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentene, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, heptenyl, adamantyl, norbornyl (or bicyclo [2.2.1] heptanyl), norbornyl, bicyclo [1.1.1] pentanyl, bicyclo [2.1.1] hexanyl, bicyclo [2.2.2] octanyl or phenyl,
t2 groups may be furyl, thienyl, 1H-pyrrolyl, silol, borolpentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilol, azaborol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl,
the T3 group may be furyl, thienyl, 1H-pyrrolyl, silol or borolopentadienyl, and
the T4 group may be a 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilol, azaborol, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl group.
As used herein, the term "cyclic group, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, pi-electron rich C 3 -C 60 Nitrogen-containing C with cyclic or pi-electron deficient groups 1 -C 60 A cyclic group "refers to a group that is fused to any cyclic, monovalent, or multivalent group (e.g., divalent, trivalent, tetravalent, etc.) according to the structure of the formula in which the corresponding term is used. For example, "phenyl"And may be benzo, phenyl, and/or phenylene, etc., as would be readily understood by one of ordinary skill in the art based on the structure of the formula including "phenyl".
Monovalent C 3 -C 60 Carbocyclyl and monovalent C 1 -C 60 Examples of heterocyclyl groups may be C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, and/or monovalent non-aromatic fused heteropolycyclic groups. Divalent C 3 -C 60 Carbocyclyl and divalent C 1 -C 60 Examples of heterocyclyl groups may be C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenyl ene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene group, C 1 -C 60 Heteroarylene, divalent non-aromatic fused polycyclic groups, and/or divalent non-aromatic fused heteropolycyclic groups.
As used herein, the term "C 1 -C 60 Alkyl "refers to a straight or branched chain aliphatic hydrocarbon monovalent radical having 1 to 60 carbon atoms, e.g., C 1 -C 20 Alkyl, and specific examples thereof may be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji and/or tert-decyl. As used herein, the term "C 1 -C 60 Alkylene "means having a structural formula corresponding to C 1 -C 60 Divalent groups of the same structure as the alkyl group.
As used herein, the term "C 2 -C 60 Alkenyl "means at C 2 -C 60 Having at least one alkyl group in the middle or at the endA monovalent hydrocarbon group of one carbon-carbon double bond, and examples thereof may be vinyl, propenyl, and/or butenyl. As used herein, the term "C 2 -C 60 Alkenylene means having a radical corresponding to C 2 -C 60 Alkenyl groups are divalent radicals of the same structure.
As used herein, the term "C 2 -C 60 Alkynyl "means at C 2 -C 60 Monovalent hydrocarbon groups having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, and examples thereof are acetylene groups and/or propynyl groups and the like. As used herein, the term "C 2 -C 60 Alkynylene "means having a radical similar to C 2 -C 60 Alkynyl groups are divalent radicals of the same structure.
As used herein, the term "C 1 -C 60 Alkoxy "means a radical derived from-OA 101 Represented monovalent groups (wherein A 101 Is C 1 -C 60 Alkyl), and examples thereof may include methoxy, ethoxy, and/or isopropoxy.
As used herein, the term "C 3 -C 10 Cycloalkyl "refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo [ 2.2.1)]Heptyl), bicyclo [1.1.1]Amyl, bicyclo [2.1.1 ]]Hexyl and/or bicyclo [2.2.2]Octyl. As used herein, the term "C 3 -C 10 Cycloalkylene "means having a structure similar to C 3 -C 10 Cycloalkyl groups are divalent radicals of the same structure.
As used herein, the term "C 1 -C 10 Heterocycloalkyl "means a monovalent cyclic group of 1 to 10 carbon atoms further comprising at least one heteroatom as a ring-forming atom in addition to carbon atoms, and specific examples are 1,2,3, 4-oxatriazolyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 Heterocyclylene "means having a radical corresponding to C 1 -C 10 Divalent groups of the same structure as the heterocycloalkyl group.
As hereinThe term "C", as used herein 3 -C 10 Cycloalkenyl "refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and no aromaticity, and specific examples thereof are cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 Cycloalkenyl "means having a structural formula with C 3 -C 10 Divalent groups of the same structure as cycloalkenyl groups.
As used herein, the term "C 1 -C 10 Heterocycloalkenyl "refers to a monovalent cyclic group of 1 to 10 carbon atoms that further includes at least one heteroatom in its ring structure as a ring-forming atom, and that has at least one double bond. C (C) 1 -C 10 Examples of heterocycloalkenyl groups include 4, 5-dihydro-1, 2,3, 4-oxazolyl, 2, 3-dihydrofuranyl, and 2, 3-dihydrothiophenyl. As used herein, the term "C 1 -C 10 Heterocycloalkenylene "means having a structure similar to C 1 -C 10 Divalent groups of the same structure as the heterocycloalkenyl group.
As used herein, the term "C 6 -C 60 Aryl "refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term" C 6 -C 60 Arylene "refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. C (C) 6 -C 60 Examples of aryl groups are phenyl, pentylene, naphthyl, azulenyl, indacenyl, acenaphthylene, phenalenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1, 2-benzophenanthryl, perylenyl, pentylphenyl, heptenyl, tetracenyl, picene, hexaphenyl, pentacenyl, yured province, coronenyl, egg phenyl, fluorenyl, spirobifluorenyl and/or benzofluorenyl. When C 6 -C 60 Aryl and C 6 -C 60 Where arylene groups each include two or more rings, the rings may be fused to each other.
As used herein, the term "C 1 -C 60 Heteroaryl "means a compound having 1 to 60 carbon atoms which further comprises at least one heteroatom as a ring-forming atom in addition to carbon atomsMonovalent groups of heterocyclic aromatic systems. As used herein, the term "C 1 -C 60 Heteroarylene "refers to a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms further comprising at least one heteroatom as a ring-forming atom in addition to carbon atoms. C (C) 1 -C 60 Examples of heteroaryl groups are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, azafluorenyl, carbazolyl, azacarbazolyl, indenocarzolyl, indolocarzolyl, benzofuranocarzolyl, benzothiophenocarzolyl, benzosiloxazolyl, benzoindolocarzolyl and/or benzocarbazolyl. When C 1 -C 60 Heteroaryl and C 1 -C 60 Where the heteroarylene groups each include two or more rings, the rings may be fused to each other.
As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure (e.g., having 8 to 60 carbon atoms). Examples of monovalent non-aromatic fused polycyclic groups are indenyl, indenofenyl and/or indenofrenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic groups described above.
As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other that further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, and that is free of aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphtalindolyl, isoindolyl, benzindolyl, benzisoxazolyl, benzothienyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, benzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, benzonaphtalenyl, benzothiophenyl, benzonaphtalenothioyl, benzofuranyl, benzodibenzofuranyl, dibenzofuranyl and/or benzothiophenyl. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic groups described above.
As used herein, the term "C 6 -C 60 Aryloxy "indicates-OA 102 (wherein A 102 Is C 6 -C 60 Aryl), and as used herein, the term "C 6 -C 60 Arylthio "indicating-SA 103 (wherein A 103 Is C 6 -C 60 Aryl).
As used herein, the term "R 10a "means:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or a combination of one or more of them,
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof, or
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 )，
Q as used herein 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently can be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl, C 1 -C 60 C substituted by heterocyclyl or one or more combinations thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl group、C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms are O, S, N, P, si, B, ge, se and one or more combinations thereof.
"Ph" as used herein refers to phenyl, "Me" as used herein refers to methyl, "Et" as used herein refers to ethyl, "tert-Bu" or "Bu" as used herein t "refers to tert-butyl, and" OMe "as used herein refers to methoxy.
As used herein, the term "biphenyl" refers to "phenyl substituted with phenyl. For example, "biphenyl" may be a compound having C 6 -C 60 Substituted phenyl groups with aryl groups as substituents.
As used herein, the term "terphenyl" refers to "phenyl substituted with biphenyl". For example, "terphenyl" may be a compound having a quilt C 6 -C 60 Aryl substituted C 6 -C 60 Substituted phenyl groups with aryl groups as substituents.
As used herein, unless otherwise defined, each refers to a bonding site with an adjacent atom in the corresponding formula.
Hereinafter, the compound according to the embodiment and the light emitting device according to the embodiment will be described in more detail with reference to the following synthesis examples and examples. The expression "using B instead of a" used in describing the synthesis examples indicates that the same molar equivalent of B is used instead of a.
Examples
Synthesis example 1: synthesis of Compound 1
Figure BDA0003941374030000711
Synthesis of intermediate A-1
20g (1.36 mol) ofPyrido [1,2-a ]]Indole was dissolved in 200mL of dichloromethane (MC), and 20mL of N-bromosuccinimide (NBS) dissolved in MC was slowly added thereto at room temperature. When the reaction was completed after stirring for 10 hours and adding water thereto, the reaction product was subjected to an extraction process with diethyl ether and washed three times with water. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. In this regard, the obtained reaction product was purified by silica gel column chromatography to obtain 23.4g of intermediate A-1 in 80% yield. (C) 12 H 8 BrN：M+1 247.1)
Synthesis of intermediate A-2
23g (93.5 mmol) of intermediate A-1 was dissolved in 30mL of Tetrahydrofuran (THF), and 44.0mL of n-butyllithium (2.5M in n-hexane, 110 mmol) was slowly added thereto at a temperature of-78 ℃. After 1 hour 30 minutes, 24.0mL (120 mmol) of 2-isopropoxy-4, 5-tetramethyl-1, 3, 2-dioxaborolan was added thereto. After the temperature was raised to room temperature and the reaction product was stirred for 4 hours and the reaction was completed by adding water thereto, the reaction product was extracted with diethyl ether and washed three times with water. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. In this regard, the obtained reaction product was purified by silica gel column chromatography to obtain 21.6g of intermediate A-2 in 79% yield. (C) 18 H 20 BNO 2 ：M+1 294.1)
Synthesis of intermediate A-3
In the presence of 21g of intermediate A-2 (71.6 mmol), 18.4g (81.4 mmol) of 2, 4-dichloro-6-phenyl-1, 3, 5-triazine, 4.80g (4.15 mmol) of tetrakis triphenylphosphine palladium, 1.33g of tetrabutylammonium bromide (4.15 mmol) and 52.9g (249 mmol) of K 3 PO 4 Dissolved in 830mL of a mixed solution comprising toluene/ethanol/water (3/3/1 by volume) and the reaction product was stirred by using a reflux condenser at a temperature of 100 ℃. After 12 hours, the reaction solution was cooled to room temperature and an extraction process with diethyl ether and water was performed. In this regard, the obtained reaction product was purified by silica gel column chromatography to obtain 18.9g of intermediate A-3 in a yield of 74%. (C) 21 H 13 ClN 4 ：M+1 357.8)
Synthesis of Compound 1
18g (50.4 mmol) of intermediate A-3 and 14g (30.3 mmol) of intermediate B-1 were dissolved in 200mL of THF, and 4.40mL of n-butyllithium (2.5M in n-hexane, 11.0 mmol) was slowly added thereto at a temperature of-78 ℃. After 1 hour and 30 minutes, 19.32g (72.0 mmol) of fluorous-di-mesitylene borane dissolved in 100mL of THF was added thereto. After the temperature was raised to room temperature and the reaction product was stirred for 6 hours and the reaction was completed by adding water thereto, the reaction product was extracted with diethyl ether and washed three times with water. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. In this regard, the obtained reaction product was purified by silica gel column chromatography to obtain 19.8g of compound 1 in a yield of 60%. (C) 45 H 32 N 4 Si：M+1 657.8)
Synthesis example 2: synthesis of Compound 2
Figure BDA0003941374030000721
Compound 2 was synthesized in substantially the same manner and molar ratio as the synthesis process of compound 1, with a yield of 75%, except that intermediate B-2 was used instead of intermediate B-1. (C) 45 H 32 N 4 Si：M+1 657.8)
Synthesis example 3: synthesis of Compound 3
Figure BDA0003941374030000722
Compound 3 was synthesized in substantially the same manner and molar ratio as the synthesis process of compound 1, with a yield of 60%, except that intermediate B-3 was used instead of intermediate B-1. (C) 45 H 32 N 4 Si：M+1 657.8)
Synthesis example 4: synthesis of Compound 5
Figure BDA0003941374030000731
Synthesis of intermediate C-1
Intermediate C-1 was synthesized in substantially the same manner as in the synthesis process of intermediate A-3, with a yield of 60%.
Synthesis of Compound 5
Compound 5 was synthesized in substantially the same manner and molar ratio as the synthesis process of compound 2, with a yield of 55%, except that intermediate C-1 was used instead of intermediate a-3. (C) 51 H 36 N 4 Si：M+1 733.9)
Table 1 shows the synthesized compounds 1 H NMR and MS/FAB. By referring to the synthetic routes and raw materials described above, one skilled in the art can readily recognize synthetic methods for compounds other than those shown in table 1.
TABLE 1
Figure BDA0003941374030000732
Example 1
As an ITO anode, a substrate having 15 Ω/cm thereon was used 2
Figure BDA0003941374030000733
The glass substrate of ITO (manufactured by corning corporation) was cut into a size of 50mm×50mm×0.7mm, sonicated with isopropyl alcohol and pure water each for 15 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resulting glass substrate was loaded onto a vacuum deposition apparatus.
Vacuum depositing 2-TNATA on ITO anode formed on glass substrate to form a film with a thickness of
Figure BDA0003941374030000741
And then, vacuum depositing NPB on the hole injection layer to form a layer having a thickness +>
Figure BDA0003941374030000742
Is provided.
Compound 1 and BCPDS (1:1 weight ratio) were co-deposited as host and PD17 as dopant at a weight ratio of 90:10Is deposited on the hole transport layer to form a film of a thickness of
Figure BDA0003941374030000743
Is provided. />
Subsequently, TSPO1 is deposited on the emissive layer to form a thickness of
Figure BDA0003941374030000744
Is a hole blocking layer of Alq 3 Deposited on the hole blocking layer to form a thickness +.>
Figure BDA0003941374030000745
Is deposited to form LiF with thickness
Figure BDA0003941374030000746
And Al is vacuum deposited thereon to form an electron injection layer having a thickness of +>
Figure BDA0003941374030000747
To complete the manufacture of the light emitting device.
Figure BDA0003941374030000748
Examples 2 and 3 and comparative examples 1 to 3
A light-emitting device was manufactured in substantially the same manner as in example 1 except that the compounds shown in table 2 were used as a main body in forming an emission layer.
Example 4
As an ITO anode, a substrate having 15 Ω/cm thereon was used 2
Figure BDA0003941374030000749
The glass substrate of ITO (manufactured by corning corporation) was cut into a size of 50mm×50mm×0.7mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then the obtained glass substrate is loaded into Vacuum deposition equipment.
Vacuum depositing NPB on ITO anode formed on glass substrate to form a film with thickness of
Figure BDA0003941374030000751
And then, vacuum depositing mCP on the hole injection layer to form a layer having a thickness +>
Figure BDA0003941374030000752
Is provided.
Compound 2 as host and ACRSA as dopant were co-deposited on the hole transport layer in a weight ratio of 92:8 to form a thickness of
Figure BDA0003941374030000753
Is provided.
Subsequently, DPEPO is deposited on the emission layer to form a layer with a thickness of
Figure BDA0003941374030000754
Is deposited on the electron transport layer to form LiF having a thickness +.>
Figure BDA0003941374030000755
And vacuum depositing Al thereon to form a layer of a thickness of
Figure BDA0003941374030000756
To complete the manufacture of the light emitting device. />
Figure BDA0003941374030000757
Example 5 and comparative examples 4 and 5
A light-emitting device was manufactured in substantially the same manner as in example 4 except that the compounds shown in table 2 were used as a main body in forming an emission layer.
Evaluation example 1
To evaluateThe characteristics of the light emitting devices manufactured according to examples 1 to 5 and comparative examples 1 to 5 were measured at 50mA/cm 2 Drive voltage at current density, luminance, luminous efficiency and at 100mA/cm 2 Is a half-life at current density. The driving voltage of the light emitting device was measured using a source meter (Keithley Instrument company, 2400 series). Quantum efficiency was measured using a Quantum efficiency measurement device C9920-2-12 from Hamamatsu Photonics. In the evaluation of quantum efficiency, brightness/current density was measured using a brightness meter calibrated for wavelength sensitivity. Half-life is a measure of the time (hours) required for the luminance to reach 50% of the original luminance. Table 2 shows the evaluation results of the characteristics of the light emitting device.
TABLE 2
Figure BDA0003941374030000761
Figure BDA0003941374030000762
As can be seen from table 2, the light emitting devices of examples 1 to 5 each show a low driving voltage, excellent or appropriate luminance, light emitting efficiency, and half-life, as compared with the light emitting devices of comparative examples 1 to 5.
Although the present disclosure has been described with reference to synthesis examples and embodiments, these embodiments are provided for illustrative purposes only and those of ordinary skill in the art will appreciate that these embodiments may have one or more suitable modifications and other embodiments equivalent thereto. Accordingly, the scope of the present disclosure should be determined by the technical concept of the claims, but is not limited thereto.
The heterocyclic compound represented by formula 1 can be used to manufacture a light-emitting device having high light-emitting efficiency and long lifetime, and the light-emitting device can be used to manufacture high-quality electronic equipment having high light-emitting efficiency and long lifetime.
The use of "may" when describing embodiments of the present disclosure refers to "one or more embodiments of the present disclosure.
As used herein, the terms "substantially," "about," and similar terms are used as approximate terms and not as degree terms, and are intended to account for inherent deviations in measured or calculated values that one of ordinary skill in the art would recognize. As used herein, "about" or "approximately" includes the recited values and means within an acceptable range of deviation of the particular value as determined by one of ordinary skill in the art in view of the measurements in question and the errors associated with the particular number of measurements (i.e., limitations of the measurement system). For example, "about" may mean within one or more standard deviations of the stated values, or within ±30%, ±20%, ±10% or ±5% of the stated value.
Also, any numerical range recited herein is intended to include all sub-ranges having the same numerical accuracy as if they were within the range recited. For example, a range of "1.0 to 10.0" is intended to include all subranges between the minimum value of 1.0 recited and the maximum value of 10.0 recited (and including 1.0 and 10.0), i.e., having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation set forth herein is intended to include all lower numerical limitations falling therein and any minimum numerical limitation set forth in the present disclosure is intended to include all higher numerical limitations falling therein. Accordingly, the applicant reserves the right to modify the present disclosure including the claims to expressly state any subranges falling within the range expressly set forth herein.
The electronic devices, light emitting devices, and/or any other related apparatus or component of the present disclosure described herein according to embodiments may be implemented using any suitable hardware, firmware (e.g., application specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one Integrated Circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, tape Carrier Package (TCP), printed Circuit Board (PCB), or formed on one substrate. Further, the various components of the apparatus may be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions, and interacting with other system components for performing the various functions described herein. The computer program instructions are stored in a memory that may be implemented in a computing device using standard storage devices such as, for example, random Access Memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM or flash memory drive, etc. Also, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or that the functionality of a dedicated computing device may be distributed over one or more other computing devices, without departing from the scope of embodiments of the present disclosure.
It should be understood that the embodiments described herein should be considered in descriptive sense only and not for purposes of limitation. The description of features or aspects in each embodiment should generally be considered other similar features or aspects that may be used in other embodiments of the present disclosure. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims and their equivalents.

Claims (20)

1. A light emitting device, comprising:
the first electrode is arranged to be electrically connected to the first electrode,
a second electrode facing the first electrode,
an interlayer between the first electrode and the second electrode and comprising an emissive layer; and
at least one heterocyclic compound represented by formula 1:
1 (1)
Figure FDA0003941374020000011
2, 2
Figure FDA0003941374020000012
Wherein, in the formulas 1 and 2,
A 1 is C 3 -C 60 Carbocyclyl or C 1 -C 60 Heterocyclyl, and A 2 Is C 1 -C 60 A heterocyclic group,
L 1 to L 3 Each independently being unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
a1 to a3 are each independently an integer selected from 0 to 3,
R 1 To R 3 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 )、-P(＝O)(Q 1 )(Q 2 ) Or a group represented by the formula 2,
n1 and n2 are each independently an integer selected from 1 to 10,
n 1R in 1 1 N 2R 2 And R is 3 At least one of which is a group represented by formula 2,
Ar 1 to Ar 3 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
* Indicating the bonding sites with adjacent atoms,
R 10a the method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or one or more combinations thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) And (2) and
wherein Q is 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl, C 1 -C 60 C substituted by heterocyclyl or one or more combinations thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
2. The light-emitting device of claim 1, wherein
The first electrode is an anode and the second electrode is an anode,
the second electrode is a cathode electrode and,
the interlayer further comprises a hole transport region between the emissive layer and the first electrode,
the interlayer further comprises an electron transport region between the emissive layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or one or more combinations thereof, and
the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or one or more combinations thereof.
3. The light-emitting device according to claim 1, wherein the emission layer comprises at least one heterocyclic compound represented by formula 1.
4. The light emitting device of claim 1, wherein the emissive layer is configured to emit blue or blue green light.
5. An electronic device comprising the light-emitting device according to any one of claims 1 to 4.
6. The electronic device of claim 5, further comprising:
thin film transistor, wherein
The thin film transistor includes a source electrode and a drain electrode, and
the first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode.
7. The electronic device of claim 5, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or one or more combinations thereof.
8. A heterocyclic compound represented by formula 1:
1 (1)
Figure FDA0003941374020000031
2, 2
Figure FDA0003941374020000041
Wherein, in the formulas 1 and 2,
A 1 is C 3 -C 60 Carbocyclyl or C 1 -C 60 Heterocyclyl, and A 2 Is C 1 -C 60 A heterocyclic group,
L 1 to L 3 Each independently being unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 A heterocyclic group,
a1 to a3 are each independently an integer selected from 0 to 3,
R 1 to R 3 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 )、-P(＝O)(Q 1 )(Q 2 ) Or a group represented by the formula 2,
n1 and n2 are each independently an integer selected from 1 to 10,
n 1R in 1 1 N 2R 2 And R is 3 At least one of which is a group represented by formula 2,
Ar 1 to Ar 3 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Heterocyclyl, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C 6 -C 60 Arylthio, -Si (Q) 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 )，
* Indicating the bonding sites with adjacent atoms,
R 10a the method comprises the following steps:
deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or one or more combinations thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) And (2) and
wherein Q is 1 To Q 3 、Q 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; cyano group; a nitro group; or each unsubstituted or deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl, C 1 -C 60 C substituted by heterocyclyl or one or more combinations thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl.
9. The heterocyclic compound according to claim 8, wherein a 1 And A 2 Each independently is phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthrenyl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoborodopentadienyl, benzophospholanyl, indenyl, benzosilol, benzogermanopyranenyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolanyl, dibenzophospholanenyl, fluorenyl, dibenzosilol, dibenzogermanium heterocyclopentadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophen-5-oxide, 9H-fluoren-9-onyl, dibenzothiophene-5, 5-dioxide, azaindolyl, azabenzoborolanyl, azabenzophospholanyl, azaindenyl, azabenzothiophenyl, azabenzocyclopentadienyl, azabenzogermanium pentalenylAn azabenzothiophenyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborol, azadibenzophosphol, azafluorenyl, azadibenzothiazyl, azagermyl, azadibenzothiophenyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophen-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophen-5, 5-dioxide, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, tetrahydrobenzoquinolinyl, 7,8, 6-tetrahydrobenzoquinolinyl, 8, 7, 6-tetrahydroquinolinyl, 8, 6-tetrahydroquinolinyl.
10. The heterocyclic compound according to claim 8, wherein L 1 To L 3 Each independently is each unsubstituted or substituted with at least one R 10a Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophen-5-oxide, 9H-fluoren-9-onyl, dibenzothiophene-5, 5-dioxide, azaindolyl, azabenzoborolan, azabenzoazacyclopentadienyl, benzothiophenyl, azaselenophenyl, benzofuranyl, carbazolyl, dibenzoborolan, dibenzophospholanenyl, fluorenyl, dibenzosilol, dibenzogermanium cyclopentadienyl, dibenzothiophenyl, dibenzofuranyl, dibenzothiophen-5-oxide, 9H-fluoren-9-onyl, dibenzothiophen-5, 5-dioxide, azaindolyl, azabenzoborolan, azabenzophospholanyl, azaindenyl, azabenzothiophenyl, azabenzopyrrolyl, azabenzocarbazolyl, dibenzothiophenyl, azabenzoguanyl, borazine, and azabenzofuranylHeterocyclopentadienyl, azadibenzophospholanyl, azafluorenyl, azadibenzosilol, azadibenzogermanium heterocyclopentadienyl, azadibenzothiophenyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophen-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophen-5, 5-dioxide, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolyl or 5, 7, 8-tetrahydroquinolinyl.
11. The heterocyclic compound according to claim 8, wherein L 1 To L 3 Each independently is a group represented by one of formulas 3-1 to 3-41:
Figure FDA0003941374020000071
/>
Figure FDA0003941374020000081
wherein, in the formulas 3-1 to 3-41,
X 1 is N or C (Z 3 )，
X 2 Is N or C (Z 4 )，
X 3 Is N or C (Z 5 )，
X 4 Is N or C (Z 6 )，
Y 1 Is either O or S, and is preferably selected from the group consisting of,
Y 2 o, S, N (Z) 7 ) Or C (Z) 7 )(Z 8 )，
Z 1 To Z 8 Each independently of the otherThe method comprises the following steps:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
c each unsubstituted or substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 An alkoxy group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(＝O)(Q 11 )、-S(＝O) 2 (Q 11 )、-P(＝O)(Q 11 )(Q 12 ) Or one or more combinations thereof;
c each unsubstituted or substituted by 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclyl, C 1 -C 60 Heterocyclyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si (Q) 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(＝O)(Q 21 )、-S(＝O) 2 (Q 21 )、-P(＝O)(Q 21 )(Q 22 ) Or one or more combinations thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 ) or-P (=O) (Q 31 )(Q 32 ) And (2) and
wherein Q is 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 Q in each of the formulae 1 and 2 11 To Q 13 、Q 21 To Q 23 And Q 31 To Q 33 The same is true of the fact that,
e6 is an integer selected from 1 to 6,
e7 is an integer selected from 1 to 7,
e8 is an integer selected from 1 to 8, and
* And each indicates a bonding site to an adjacent atom.
12. The heterocyclic compound according to claim 8, wherein the heterocyclic compound represented by formula 1 is represented by formula 1-1:
1-1
Figure FDA0003941374020000091
And is also provided with
Wherein, in the formula 1-1,
X 11 is N or C (E 11 )，
X 12 Is N or C (E 12 )，
X 13 Is N or C (E 13 )，
X 14 Is N or C (E 14 )，
X 21 Is N or C (E 21 )，
X 22 Is N or C (E 22 )，
X 23 Is N or C (E 23 )，
X 24 Is N or C (E 24 )，
E 11 Is- (L) 11 ) a11 -R 11 ，
E 12 Is- (L) 12 ) a12 -R 12 ，
E 13 Is- (L) 13 ) a13 -R 13 ，
E 14 Is- (L) 14 ) a14 -R 14 ，
E 21 Is- (L) 21 ) a21 -R 21 ，
E 22 Is- (L) 22 ) a22 -R 22 ，
E 23 Is- (L) 23 ) a23 -R 23 ，
E 24 Is- (L) 24 ) a24 -R 24 ，
E 11 To E to 14 And E is 21 To E to 24 Optionally bonded to each other to form an unsubstituted or substituted radical with at least one R 10a Substituted C 5 -C 30 Carbocyclyl or is unsubstituted or substituted by at least one R 10a Substituted C 2 -C 30 A heterocyclic group,
L 11 to L 14 Each independently of L 1 The same is true of the fact that,
a11 to a14 are each independently the same as a1,
R 11 to R 14 Each independently of R 1 The same is true of the fact that,
L 21 to L 24 Each independently of L 2 The same is true of the fact that,
a21 to a24 are each independently the same as a2,
R 21 to R 24 Each independently of R 2 The same is true of the fact that,
L 3 、a3、R 3 and R is 10a Respectively with L defined in reference 1 3 、a3、R 3 And R is 10a The same is true of the fact that,
R 11 to R 14 、R 21 To R 24 And R is 3 At least one of them is a group represented by formula 2, and
* Indicating the bonding sites with adjacent atoms.
13. The heterocyclic compound according to claim 12, wherein
R 3 Is a group represented by formula 2; or (b)
X 24 Is C (E) 24 ) And R is 24 Is a group represented by formula 2.
14. The heterocyclic compound according to claim 12, wherein X 11 Is C (E) 11 )，X 12 Is C (E) 12 )，X 13 Is C (E) 13 )，X 14 Is C (E) 14 )，X 21 Is C (E) 21 )，X 22 Is C (E) 22 )，X 23 Is C (E) 23 ) And X is 24 Is C (E) 24 )。
15. The heterocyclic compound according to claim 8, wherein at least one of n1 a1, n2 a2 and a3 in formula 1 is an integer of 1 or more.
16. The heterocyclic compound according to claim 12, wherein the heterocyclic compound represented by formula 1-1 is represented by formula 1-2:
1-2
Figure FDA0003941374020000111
Wherein, in the formula 1-2,
X 31 is N or C (E 31 )，
X 32 Is N or C (E 32 )，
X 33 Is N or C (E 33 )，
X 34 Is N or C (E 34 )，
X 35 Is N or C (E 35 )，
E 31 Is- (L) 31 ) a31 -R 31 ，
E 32 Is- (L) 32 ) a32 -R 32 ，
E 33 Is- (L) 33 ) a33 -R 33 ，
E 34 Is- (L) 34 ) a34 -R 34 ，
E 35 Is- (L) 35 ) a35 -R 35 ，
X 11 To X 14 And X 21 To X 24 Respectively with X defined in the formula 1-1 11 To X 14 And X 21 To X 24 The same is true of the fact that,
L 31 to L 35 Each independently of L 3 The same is true of the fact that,
a31 to a35 are each independently an integer selected from 0 to 2,
R 31 to R 35 Each independently of R 3 The same is true of the fact that,
R 11 to R 14 、R 21 To R 24 And R is 31 To R 35 At least one of them is a group represented by formula 2, and
* Indicating the bonding sites with adjacent atoms.
17. The heterocyclic compound according to claim 8, wherein the sum of n1 a1, n2 a2 and a3 in formula 1 is 2 or more.
18. The heterocyclic compound according to claim 8, wherein
R 1 To R 3 Each independently is:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
c each substituted by 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, and,Cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or one or more combinations thereof;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C, each unsubstituted or substituted by 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, or azadibenzothiazyl). Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinazolinylA group selected from the group consisting of a pinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, a benzisothiazolyl group, a benzoxazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azafluorenyl group, an azadibenzosilol group, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or one or more combinations thereof;
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
A group represented by formula 2, and
wherein the method comprises the steps of
Q 1 To Q 3 And Q 31 To Q 33 Each independently is:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl each of which is unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or one or more combinations thereof.
19. The heterocyclic compound according to claim 8, wherein
Ar 1 To Ar 3 Each independently is:
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group;
c each substituted by 1 -C 20 Alkyl or C 1 -C 20 An alkoxy group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or one or more combinations thereof;
Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C, each unsubstituted or substituted by 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolylTriazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl or azadibenzosilol groups): deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, -Si (Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(＝O)(Q 31 )、-S(＝O) 2 (Q 31 )、-P(＝O)(Q 31 )(Q 32 ) Or one or more combinations thereof; or (b)
-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(＝O)(Q 1 )、-S(＝O) 2 (Q 1 ) or-P (=O) (Q 1 )(Q 2 ) And (2) and
wherein the method comprises the steps of
Q 1 To Q 3 And Q 31 To Q 33 Each independently is:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 The method comprises the steps of carrying out a first treatment on the surface of the Or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl each of which is unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or one or more combinations thereof.
20. The heterocyclic compound according to claim 8, wherein the heterocyclic compound is one of compound 1 to compound 8:
Figure FDA0003941374020000151
/>
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